N'1-[((2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidylcarbonyl)oxy]ethanimidamide → (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(3-methyl-1,2,4-oxadiazol-5-yl)piperidine

HRID 397640Notes

Reaction equation

HRID 397640 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([O:19][N:20]=[C:21]([NH2:23])[CH3:22])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]2[O:19][N:20]=[C:21]([CH3:22])[N:23]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86759129N'1-[((2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidylcarbonyl)oxy]ethanimidamide

Product 1

HCID 52104633(2S)-1-[(4-fluorophenyl)sulfonyl]-2-(3-methyl-1,2,4-oxadiazol-5-yl)piperidine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The title compound was prepared by a similar method to Preparation 6 from N′1-[((2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidylcarbonyl)oxy]ethanimidamide [see Preparation 82] and xylene. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 80:20, by volume, hexane:ethyl acetate in 10% increments, to afford (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(3-methyl-1,2,4-oxadiazol-5-yl)piperidine as an oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 80:20, by volume, hexane

Sources & evidence

ORD record
ord-4ac1838502054db385a382963e4a11aa
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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